CN109810091B - Process for the preparation of alkylene carbonate from alkylene oxide and carbon dioxide - Google Patents

Process for the preparation of alkylene carbonate from alkylene oxide and carbon dioxide Download PDF

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CN109810091B
CN109810091B CN201910122112.7A CN201910122112A CN109810091B CN 109810091 B CN109810091 B CN 109810091B CN 201910122112 A CN201910122112 A CN 201910122112A CN 109810091 B CN109810091 B CN 109810091B
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carbon dioxide
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alkylene
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CN109810091A (en
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郭建军
李新
张兴明
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Shi Dashenghua New Materials Group Co ltd
Shenghua New Energy Technology Dongying Co Ltd
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Shandong Shida Shenghua Chemical Group Co Ltd
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    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C07D317/38—Ethylene carbonate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
    • B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
    • B01J2531/26—Zinc
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms

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Abstract

The present invention relates to a process for the preparation of alkylene carbonate from alkylene oxide and carbon dioxide. The technical scheme is as follows: taking alkylene oxide and carbon dioxide as raw materials, and contacting the reaction raw materials with a catalyst to generate alkylene carbonate; the catalyst is a polybase complex compound catalytic system containing imidazole groups, salicylic acid groups and zinc, and the molar ratio of the zinc to the imidazole groups and the salicylic acid groups is 5:1-50: 1-50. The beneficial effects are that: the method adopts a polybase complex compound catalytic system containing imidazole groups, salicylic acid groups and zinc, the conversion rate of ethylene oxide is high, the selectivity of ethylene carbonate is high, and a better technical effect is obtained.

Description

Process for the preparation of alkylene carbonate from alkylene oxide and carbon dioxide
Technical Field
The invention relates to a preparation method of alkylene carbonate, in particular to a method for preparing alkylene carbonate by using alkylene oxide and carbon dioxide.
Background
The alkylene carbonate is a solvent with excellent performance and a fine chemical intermediate, and is a potential basic raw material of organic chemical industry. With CO2Is a greenhouse gas, and how to effectively fix the greenhouse gas becomes one of the most challenging problems in the century, namely, the fixation through alkylene oxide and CO2The synthesis of alkylene carbonate by reaction is a good fixing method. With the recent increasing interest in the CO-production of dimethyl carbonate and diols starting from alkylene carbonates, CO is fixed by cyclic carbonates2The approach of (a) has also received increasing attention.
Has been reported for CO2The catalyst system for the esterification reaction with EO is various and includes ammonium, onium halides of phosphorus, tributyl methyl phosphorus iodide), metal halides (such as KBr, ZnCl2Etc.), imidazole and pyridine based ionic liquids, metal complexes, amines, and polymer supported catalysts, etc. The catalytic system has low reaction activity or the product has yellow color to cause the quality reduction of the product, and the like. The alkaline earth metal salt CaCl was found by the company Olin Mathieson in U.S. Pat. No. 3,29077712The EC solution has better catalytic activity on the cycloaddition reaction of EO, and the EC yield is 68.4 percent when the reaction is continuously carried out at 800 Psi and 190 ℃. The influence of the type of alkali metal and complex on the catalyst catalyzing the EC reaction for EO synthesis was studied by Shell in US7488835, and as a result, it was found that the effect was the best when the catalyst system was KI/18-crown-6,the reaction was carried out at 80 ℃ for 1 h at 2 MPa, EO conversion was 84% and EC selectivity was 98%. The ionic liquid 1-methyl-3-butylimidazole bromide used in CN1995032 was used as a catalyst to react for 0.7 h at EO/Cat = 208, 100 oC and 2.0 MPa to give an EC yield of 92.2%.
A polybase complex compound catalytic system containing imidazole groups, salicylic acid groups and zinc is prepared, and a catalyst with good activity is obtained.
Disclosure of Invention
The present invention aims to overcome the above-mentioned defects of the prior art and provide a method for preparing alkylene carbonate from alkylene oxide and carbon dioxide, which has the characteristic of high catalyst activity.
The invention provides a method for preparing alkylene carbonate by alkylene oxide and carbon dioxide, which adopts the technical scheme that: taking alkylene oxide and carbon dioxide as raw materials, and under the conditions that the reaction temperature is 60-200 ℃, the reaction pressure is 0.1-10.0 MPa, and the mass ratio of a catalyst to the alkylene oxide is 0.001-1: 1, contacting the raw materials with the catalyst to generate alkylene carbonate; the catalyst is a polybase complex compound catalytic system containing imidazole groups, salicylic acid groups and zinc, and the molar ratio of the zinc to the imidazole groups and the salicylic acid groups is 5:1-50: 1-50.
Preferably, the catalytic system contains at least one zinc atom.
Preferably, the catalytic system contains at least one imidazole group.
Preferably, the catalytic system contains at least one salicylaldehyde group.
Preferably, the alkylene oxide is one or more of ethylene oxide, propylene oxide, epichlorohydrin and butylene oxide.
Preferably, the reaction temperature is preferably 80-160 ℃, the reaction pressure is preferably 0.5-8.0 MPa, and the mass ratio of the catalyst to the alkylene oxide is preferably 0.005-0.5: 1.
preferably, the preparation method of the catalyst comprises the following steps:
1) and at room temperature, mixing the zinc precursor with a certain amount of salicylic acid precursor, adding a solvent, stirring, and heating to obtain an intermediate product.
2) Mixing the intermediate product with the imidazolyl precursor, adding a solvent, stirring, heating, and removing the solvent to obtain a catalyst product;
in the preparation process of the catalyst, the molar ratio of the zinc precursor, the imidazolyl precursor and the salicylic acid precursor used in the steps 1) and 2) is 5:1-50: 1-50.
Preferably, in the preparation process of the catalyst, the zinc precursor used in the step 1) is an oxide or halide of zinc;
in the preparation process of the catalyst, the salicylic acid precursor used in the step 1) is salicylic acid or salicylic acid with a side chain.
Preferably, in the preparation process of the catalyst, the imidazolyl precursor used in the step 2) is imidazole or alkyl imidazole;
in the preparation process of the catalyst, the solvent used in the step 1) and the step 2) is methanol, ethanol or diethyl ether.
The invention has the beneficial effects that: the method adopts a polyradical complex compound catalytic system containing imidazole groups, salicylic acid groups and zinc, the catalyst of the invention has a reaction temperature of 130 ℃, a reaction pressure of 3.0 MPa, and a mass ratio of the catalyst to ethylene oxide of 0.05: the reaction lasts for 3 hours in 1 hour, the conversion rate of the ethylene oxide is 99.5%, the selectivity of the ethylene carbonate is 99.2%, a good technical effect is obtained, the preparation process of the catalyst system is simple, the cost is low, the activity is good, and the catalyst system can be popularized and used in the industrial production of the alkylene carbonate.
Detailed Description
The following description of the preferred embodiments of the present invention is provided for the purpose of illustration and description, and is in no way intended to limit the invention.
Example 1:
mixing 0.5 mol of zinc oxide and 0.5 mol of salicylic acid, adding 200ml of ethanol, stirring and heating to reflux for 6h, adding 0.3 mol of imidazole, mixing, stirring, heating to reflux for 6h, cooling and filtering to obtain a catalyst product A.
Example 2
Mixing 0.5 mol of zinc bromide and 0.5 mol of salicylic acid, adding 200ml of ethanol, stirring and heating to reflux for 6h, adding 0.6 mol of imidazole, mixing, stirring, heating to reflux for 6h, cooling and filtering to obtain a catalyst product B.
Example 3
Mixing 0.5 mol of zinc chloride and 0.2 mol of salicylic acid, adding 200ml of ethanol, stirring and heating to reflux for 6h, adding 1 mol of imidazole for mixing, stirring and heating to reflux for 6h, cooling and filtering to obtain a catalyst product C.
Example 4
Mixing 0.5 mol of zinc chloride and 0.3 mol of salicylic acid, adding 200ml of ethanol, stirring and heating to reflux for 6h, adding 0.2 mol of 1-methylimidazole, mixing, stirring, heating to reflux for 6h, cooling and filtering to obtain a catalyst product D.
Example 5
Mixing 0.5 mol of zinc sulfate and 0.2 mol of salicylic acid, adding 200ml of ethanol, stirring and heating to reflux for 6h, adding 0.4mol of 2-methylimidazole, mixing, stirring, heating to reflux for 6h, cooling and filtering to obtain a catalyst product E.
Example 6
Mixing 0.5 mol of zinc chloride and 0.2 mol of 3-methyl salicylic acid, adding 200ml of ethanol, stirring and heating to reflux for 6h, adding 1 mol of butylimidazole, mixing, stirring, heating to reflux for 6h, cooling and filtering to obtain a catalyst product F.
Example 7
0.5 mol of zinc nitrate and 0.2 mol of 4-methyl salicylic acid are mixed, 200ml of ethanol is added, the mixture is stirred and heated to reflux for 6h, 0.7 mol of imidazole is added, the mixture is stirred, heated and refluxed for 6h, and the catalyst product G is obtained after cooling and filtering.
Example 8
Mixing 0.5 mol of zinc chloride and 0.2 mol of salicylic acid, adding 200ml of ethanol, stirring and heating to reflux for 6H, adding 0.2 mol of imidazole, mixing, stirring, heating to reflux for 6H, cooling and filtering to obtain a catalyst product H.
Comparative example 1
Mixing 0.5 mol of zinc bromide and 0.2 mol of salicylic acid, adding 50ml of ethanol, stirring and heating to reflux for 6h, cooling and filtering to obtain a solid intermediate product, thus obtaining a catalyst product I.
Comparative example 2
Mixing 0.5 mol of zinc bromide and 0.2 mol of imidazole, adding 50ml of ethanol, stirring and heating to reflux for 6h, cooling and filtering to obtain a catalyst product J.
Comparative example 3
Mixing 0.2 mol of salicylic acid and 0.2 mol of imidazole, adding 50ml of ethanol, stirring and heating to reflux for 6 hours, and removing the ethanol to obtain a catalyst product K.
Three comparative examples in comparison with example 8, comparative example 1 obtained a catalyst product I obtained with two compositions, the ethylene oxide conversion C of which was determined with reference to the table belowEO28.6% ethylene carbonate selectivity SEC24.8 percent; comparative example 2 obtained using two compositions a catalyst product J was obtained, which was measured for ethylene oxide conversion C, with reference to the table belowEOAt 47%, ethylene carbonate selectivity SEC99 percent; comparative example 3 obtained using two compositions a catalyst product K was obtained, which was measured for the ethylene oxide conversion C, with reference to the table belowEO4.2% ethylene carbonate selectivity SECAt 56.3%, it can be seen that the ethylene oxide conversion C is compared to the catalyst product H in example 8EO99.7% ethylene carbonate selectivity SEC99.6 percent, and the effect difference is obvious.
Example 9:
adding 0.05 g of catalyst A and 20 mL (0.4 mol) of ethylene oxide into a 100 mL stainless steel autoclave in sequence, sealing the autoclave, filling carbon dioxide with proper pressure, and slowly raising the temperature to 140 ℃ by using a temperature controlleroC, then controlling the reaction pressure to be 2.0 MPa, and reacting for 2.0 h. After the reaction, the reaction kettle is cooled, and excessive CO is slowly discharged2Opening the reaction kettle, taking a small amount of samples, performing chromatographic analysis, and measuring the conversion rate CP of the propylene oxideO99.5% ethylene carbonate selectivity SECThe content was 99.8%.
Example 10
At 100Adding 0.05 g of catalyst A and 20 mL (0.4 mol) of propylene oxide into a mL stainless steel autoclave in sequence, sealing the autoclave, filling carbon dioxide with proper pressure, and slowly raising the temperature to 120 ℃ by using a temperature controlleroC, then controlling the reaction pressure to be 2.0 MPa, and reacting for 2.0 h. After the reaction, the reaction kettle is cooled, and excessive CO is slowly discharged2Opening the reaction kettle, taking a small amount of samples, performing chromatographic analysis, and measuring that the conversion rate of the propylene oxide is 99.5 percent and the selectivity S of the propylene carbonate isECThe content was 99.4%.
Example 11
Adding 0.05 g of catalyst A and 20 mL (0.4 mol) of epichlorohydrin into a 100 mL stainless steel autoclave in sequence, sealing the autoclave, filling carbon dioxide with proper pressure, and slowly raising the temperature to 120 ℃ by using a temperature controlleroC, then controlling the reaction pressure to be 2.0 MPa, and reacting for 2.0 h. After the reaction, the reaction kettle is cooled, and excessive CO is slowly discharged2Opening the reaction kettle, taking a small amount of sample, performing chromatographic analysis, and measuring the conversion rate of the epichlorohydrin to be 99.3 percent and the selectivity S of the chlorinated propylene carbonateECThe content was 99.8%.
Example 12
The catalytic reaction of ethylene oxide and carbon dioxide was carried out in the same manner as in example 9, with the catalyst sample and the amount thereof used, and the reaction pressure being varied, and the reaction results obtained are shown in Table 1.
TABLE 1
Figure 428869DEST_PATH_IMAGE001
Examples 27 to 34
The catalytic reaction of propylene oxide with carbon dioxide was carried out in the same manner as in example 10 except that the catalyst sample used was changed and propylene oxide was used as a raw material, and the reaction results obtained are shown in Table 2.
TABLE 2
Figure 824078DEST_PATH_IMAGE002
The examples of the invention show that the performance of the comparably improved catalysts, in terms of activity or selectivity, is increased in the results list.
The above description is only a few of the preferred embodiments of the present invention, and any person skilled in the art may modify the above-described embodiments or modify them into equivalent ones. Therefore, any simple modifications or equivalent substitutions made in accordance with the technical solution of the present invention are within the scope of the claims of the present invention.

Claims (2)

1. A process for the preparation of alkylene carbonate from alkylene oxide and carbon dioxide, characterized in that: adding 0.05 g of catalyst F and 20 mL of ethylene oxide into a 100 mL stainless steel autoclave in sequence, sealing the autoclave, filling carbon dioxide with proper pressure, and slowly raising the temperature to 140 ℃ by using a temperature controlleroC, then controlling the reaction pressure to be 1.0 MPa, and reacting for 2.0 h; after the reaction, the reaction kettle is cooled, and excessive CO is slowly discharged2Opening the reaction kettle, taking a small amount of samples, performing chromatographic analysis, and measuring the conversion rate CP of the propylene oxideO99.6% ethylene carbonate selectivity SEC99.6 percent;
the preparation method of the catalyst F comprises the following steps: mixing 0.5 mol of zinc chloride and 0.2 mol of 3-methyl salicylic acid, adding 200ml of ethanol, stirring and heating to reflux for 6h, adding 1 mol of butylimidazole, mixing, stirring, heating to reflux for 6h, cooling and filtering to obtain a catalyst product F.
2. A process for the preparation of alkylene carbonate from alkylene oxide and carbon dioxide, characterized in that: adding 0.05G of catalyst G and 20 mL of ethylene oxide into a 100 mL stainless steel autoclave in sequence, sealing the autoclave, filling carbon dioxide with proper pressure, and slowly raising the temperature to 140 ℃ by using a temperature controlleroC, controlling the reaction pressure to be 2.0 MPa, and reacting for 2.0 h; after the reaction, the reaction kettle is cooled, and excessive CO is slowly discharged2Opening the reaction kettle, taking a small amount of samples, performing chromatographic analysis, and measuring the conversion rate CP of the propylene oxideO99.8% ethylene carbonate selectivity SEC99.7 percent;
the preparation method of the catalyst G comprises the following steps: 0.5 mol of zinc nitrate and 0.2 mol of 4-methyl salicylic acid are mixed, 200ml of ethanol is added, the mixture is stirred and heated to reflux for 6h, 0.7 mol of imidazole is added, the mixture is stirred, heated and refluxed for 6h, and the catalyst product G is obtained after cooling and filtering.
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CN109867654B (en) * 2019-02-19 2021-06-29 胜华新能源科技(东营)有限公司 Method for preparing alkylene carbonate from alkylene oxide and carbon dioxide
CN113877634B (en) * 2020-07-02 2023-08-29 中国石油化工股份有限公司 Catalyst, preparation method and application thereof, and method for preparing unsaturated carbonate
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US2907771A (en) 1957-12-05 1959-10-06 Olin Mathieson Ethylene carbonate
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PE20070477A1 (en) 2005-08-02 2007-05-16 Shell Int Research PROCESS FOR THE PREPARATION OF ALKYLENE CARBONATES
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Address after: 257000 Building 5, Houli village, Yong'an Town, Kenli District, Dongying City, Shandong Province

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Address after: 198 Tongxing Road, Kenli District, Dongying City, Shandong Province

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Address before: 257000 Building 5, Houli village, Yong'an Town, Kenli District, Dongying City, Shandong Province

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